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Details

Stereochemistry ABSOLUTE
Molecular Formula C60H92N12O10
Molecular Weight 1141.4469
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GRAMICIDIN S

SMILES

[H][C@@]12CCCN1C(=O)[C@@H](CC3=CC=CC=C3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@@H](NC(=O)[C@]4([H])CCCN4C(=O)[C@@H](CC5=CC=CC=C5)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN)NC(=O)[C@@H](NC2=O)C(C)C)C(C)C

InChI

InChIKey=IUAYMJGZBVDSGL-XNNAEKOYSA-N
InChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1

HIDE SMILES / InChI
Molecular Formula C60H92N12O10
Molecular Weight 1141.4469
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Gramicidin S molecule is amphiphilic, with hydrophobic amino acids (D-Phe, Val, Leu side chains) and charged aminoacid (L-Orn). It exhibits strong antibiotic activity towards Gram-negative and Gram-positive and even several pathogenic fungi. The mode of action is not entirely agreed upon, but it is disruption of the lipid membrane and enhancement of the permeability of the bacterial cytoplasmic membrane. Unfortunately, being hemolytic at even low concentrations, gramicidin S is only used as topical applications at present. Additionally, Gramicidin S has been employed as a spermicide and therapeutic for genital ulcers caused by sexually transmitted disease.

Originator

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
Curative
Approved
8429
Gramicidin S

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
EXPERIMENTAL AND CLINICAL STUDIES ON GRAMICIDIN.
1941 Sep
[Chemical nature of gramicidin C].
1945

Sample Use Guides

In Vivo Use Guide
Alcoholic preparation solution (2%)
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:05:03 UTC 2023
Edited
by admin
on Fri Dec 15 18:05:03 UTC 2023
Record UNII
WHM29QA23F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GRAMICIDIN S
INN   MART.   MI   WHO-DD  
INN  
Official Name English
CYCLO(L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL)
Common Name English
Gramicidin s [WHO-DD]
Common Name English
CYCLO(L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL-L-LEUCYL-D-PHENYLALANYL-L-PROLYL-L-VALYL-L-ORNITHYL)
Common Name English
gramicidin s [INN]
Common Name English
GRAMICIDIN S 1
Common Name English
GRAMICIDIN S [MART.]
Common Name English
GRAMICIDIN C
Common Name English
GRAMICIDIN S [MI]
Common Name English
GRAMICIDIN S-A
Common Name English
GRAMMIDIN
Brand Name English
Code System Code Type Description
MERCK INDEX
m5837
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY Merck Index
INN
3052
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
NCI_THESAURUS
C170034
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL373496
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
CHEBI
5530
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
WIKIPEDIA
GRAMICIDIN S
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
EVMPD
SUB07963MIG
Created by admin on Fri Dec 15 18:05:03 UTC 2023 , Edited by admin on Fri Dec 15 18:05:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID6046008
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
FDA UNII
WHM29QA23F
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
CAS
113-73-5
Created by admin on Fri Dec 15 18:05:03 UTC 2023 , Edited by admin on Fri Dec 15 18:05:03 UTC 2023
PRIMARY
PUBCHEM
73357
Created by admin on Fri Dec 15 18:05:04 UTC 2023 , Edited by admin on Fri Dec 15 18:05:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of GRAMICIDIN S HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of GRAMICIDIN S
ACTIVE MOIETY
NIH
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